Hydroxyamine hydrochloride → HCID 9906336, compound

Participants

Reaction Steps

To a solution of 6,6-dimethyl-5-hydroxymethylene-3-methylthio-1-(pyrrolidin-1-ylcarbonyl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (173 mg, 0.49 mmol) in EtOH (4 mL) and water (0.7 mL) was added hydroxylamine hydrochloride (38 mg, 0.54 mmol). The solution was heated at reflux for 2 h then cooled to room temperature and the solvent evaporated. The residue was partitioned between EtOAc (20 mL) and water (20 mL), the organic layer separated, dried (Na2SO4) and evaporated. The residue was triturated with hexane/Et2O and the resultant yellow solid (131 mg, 77%) collected by filtration. mp 114-116° C. C17H2ON20N2S2O2.0.1(H2O) requires: C, 58.29; H, 5.81; N, 8.00%. Found: C, 58.05; H, 5.59; N, 7.65%. 1H NMR (360 MHz, CDCl3) δ1.26 (6H, s), 1.94-1.98 (4H, m), 2.63 (3H, s), 2.90 (2H, s), 3.56-3.67 (4H, m), 8.20 (1H, s). MS (ES+) 349 (M+1).

Provenance & Evidence